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Trifluoroacetic acid → HCID 69096290, 화합물

HRID 1257153
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HRID 1257153 반응식
COC1C=CC([CH2:7][N:8](C)[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([C:21]4[CH:26]=[C:25]([NH2:27])[C:24]([F:28])=[CH:23][C:22]=4[Cl:29])[C:15](=[O:20])[N:16]3[CH3:19])=[CH:11][N:10]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][C:25]1[C:24]([F:28])=[CH:23][C:22]([Cl:29])=[C:21]([C:14]2[C:15](=[O:20])[N:16]([CH3:19])[C:17]3[C:12]([CH:13]=2)=[CH:11][N:10]=[C:9]([NH:8][CH3:7])[CH:18]=3)[CH:26]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 69296325HCID 69296325, 화합물

생성물 1

HCID 69096290HCID 69096290, 화합물수율 72.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 6.6 mmol) in DCM (50 mL) was treated with TFA (20 mL) and the mixture was heated to reflux overnight. The mixture was concentrated under reduced pressure, the residue was dissolved in 10% HCl (50 mL), washed with EtOAc, neutralized with satd. NaHCO3 and extracted with EtOAc (3×). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo to give 3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (1.6 g, 72% yield) 1H NMR (300 MHz, DMSO-d6): δ 8.36 (s, 1H), 7.66 (s, 1H), 7.17 (d, J=10.8 Hz, 1H), 7.05 (m, 1H), 6.71 (d, J=9.6 Hz, 1), 6.15 (s, 1H), 5.30 (s, 2H), 3.47 (s, 3H), 3.42 (s, 1H), 2.84 (d, J=4.4 Hz, 3H); MS (ESI) m/z: 333.1 [M+H]+

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 10% HCl (50 mL)
  5. washwashed with EtOAc
  6. extractionNaHCO3 and extracted with EtOAc (3×)
  7. washThe combined organics were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-737ac3fe9ca44fc7b250e79368e4f262
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461179B1

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